Holiday rentals with outdoor seating in Nantucket County

South of Town Surf Shack. Best Deal on Island.

Redecorated for summer 2025 with new linens and Casper beds! While the exterior is the picture perfect Nantucket cottage home surrounded by hydrangeas, you will be surprised by the casual, surf-vibe of the decor. Enjoy the best of Nantucket by walking to Town (under 1 mi) at this prime location property. The lot has privacy hedges and borders conservation land. This property has a separate living area home to two of the homeowner's employees. No parties, dinner parties, or events are allowed.

Attractive 3 Bedroom/2 Bath in Town

Enjoy walking proximity to downtown, shopping, dining, bike paths and more. Sun-splashed and comfortable, this updated cottage is in impeccable condition, tastefully decorated and fully stocked. The first floor suite has a queen bed and bath. Second floor has two bedrooms (one double bed and one two single beds), a shared bathroom and laundry. The private backyard has a patio with a sectional sofa and dining table. Outdoor shower. Central air with individual room control. All linens supplied.

Beach "Loft"

Enjoy The Beach Loft Apartment's convenient proximity to beaches, town and S’conset. Located 4 miles from the ctr. of the Historic District and 1 mile to Nobadeer beach our lofty spacious 900 sq. ft., 10 foot ceiling height apartment is the lower level (basement) of our home. Yet you will have complete privacy with separate parking as well as separate entrance and your own outdoor deck. The neighborhood is 3 acre zoning. It is secluded and quiet with many pine trees, oak and sassafras trees.

Cuddle In Cottage near Surfside Beach

This charming Nantucket chic decorated cottage is your ideal vacation spot. Perfect for 2 and a max of 4 people. The cottage is less than a mile from Surfside Beach, voted the islands favorite, and across the street from a bike path offering biking to the beach or town a safe and easy option. The cottage boasts privacy with fully stocked kitchen, in and out door shower, radiant heat, AC unit in the bedroom, 2 flat screen TV's, top drawer linens, towels, beach chairs and an out door grill.

Updated, modern and charming condo!

Updated, modern and charming condo in central Nantucket. 1,120 square feet, totally accommodates 8 people. Living room has a cozy electric fireplace for chilly Nantucket nights. Full kitchen .Lush private back yard with a patio, grill, hammock, and a relaxing outdoor shower. Two parking spots in the front of the house. Central location is walkable to downtown, grocery stores, coffee shops, restaurants, and night clubs.Close to a couple of bus stations taking you to all parts of the island.

Relaxation Awaits! Mid-Island Retreat

Our guest suite is a separate wing of the main house. It is separated by a locked door. You have your own separate private entrance. Perfect honeymoon suite. You must come into the backyard of the main house to access your suite. We do not allow pets in our guest suite. Our Airbnb is not suitable for infants or children. There is an additional guest fee of $150 per guest per night after the initial two guests. And please let us know if you are bringing a car so we can arrange parking.

Cozy cottage just off Main Street

Perfect location. Modern cottage. block off Main St. Cozy for 2, gas burning fireplace & AC. Well-equipped, open floor plan, lvg room/galley ktch/dining/ full bath WD down. Upstairs, queen bdr. and 1/2 bath. Private outdoor deck. Outdoor shower too! Beach chairs & towels, tote, cooler, umbrella, hair blower, iron. We care about the details like ironed sheets, good pillows, new mattress, & fluffy towels.! We don't provide parking & discourage bringing a car. Parking at a premium in season.

Large yard, deck & hot tub 4 bedroom, sleeps 8

**Min stay: peak season 5 nights / shoulder season 4 nights/ off season 3 nights** Tucked in off the road lies a 4 bedroom home with a spacious yard, hot tub, fire pit, and deck suitable for dining or entertaining. The modest upstairs expands to a basement with a large living area, two bedrooms, and a kitchenette. The large deck is equipped for dining or entertaining. It also features an outdoor shower for after a long day at the beach. **House is winterized for cold weather stays**

The Nantucket Farmhouse

The Nantucket Farm House was built in 1840 and was completely renovated and refurnished in 2023. If you are having trouble with ferry reservations and need a car, please let us know. We might be able to help. The home very private and is very close to beaches, bike paths, and the Nantucket public transportation stop. We are experienced Air BnB Superhosts and are committed to excellent service and guest satisfaction. We also have a full-time caretaker on island for your convenience.

Derrymore Place - an island gem

Located in a quiet neighborhood off of Cliff Road, guests can relax in a spacious 350 sq/ft beautiful bedroom with a comfortable king size bed and single day bed (w/trundle). There is a 3 piece private bathroom with washer/dryer. A full size pull out sofa is available in the very large kitchenette/game room. A 300 sq/ft comfortable sitting room with sofa, cable television, wine fridge and high top table is for your exclusive use. A private entrance allows guests to come and go freely.

Kerstin Swedish House

Enjoy this fresh 2021 new construction house tucked right in town, footsteps from boutiques, restaurants and walking distance to the Hyline ferry. The house was completely rebuilt in 2021 and has all the latest modern amenities, a sound system that links to your phone, refrigerator screen links to music and internet and a mood lighting system. Outside enjoy two patios with ceramic stone and an outdoor shower. Two smart TVs and an electric fireplace for fun add to your enjoyment!

In-Town Cottage - Walk to Shops & Restaurants!

Moongate Cottage, with quintessential Nantucket charm is walkable to downtown. Enter through the arched wooden gate in the mature hedges, to your private oasis with a quaint yard and brick patio. The cottage furnishes everything you need. From June to September, we have a 7-night minimum stay from Saturday to Saturday. Enjoy the large living room, spacious bedroom, updated kitchen and bathroom. The ambiance shows throughout with the modern beach chic decor.